Lubricant composition and method of preparing the same



Patented Feb. 14, 1939 UNITED STATES PATENT OFFICE LUBRICANT COMPOSITIONAND METHOD OF PREPARING THE SAME Mathias Pier, Heidelberg, and FriedrichChristmann, Ludwigshafen-on-the-Rhine, Germany, assignors to I. G.Farbenindustrie Aktiengesellschaft, Frankfort-on-the-Main, Germany NoDrawing. Application March 1, 1934, Seria' No. 713,601. In Germany March8, 1 933 11 Claims.

- k5 substances.

We have proposedelsewhere a process for the manufacture. and productionof lubricating oils or improving agents for lubricants from initialmaterials containing hydrocarbons which areunsuitable -for lubricatingpurposes, by halogenation and subsequent condensation in the presenceofcatalysts, the initial materials con sisting of hydrocarbons of highmolecular weight which are wholly or mainly composed of hard or softparaflin wax.

We have now found that valuable lubricating oils or products similar tolubricating oils and suitable for improving lubricants are obtained bystarting from aliphatic alcohols of high molecular weight; i; e.aliphatic hydrocarbon derivatives containing at least one hydroxylgroup', in particular those containing at least 12 carbon atoms in themolecule, and by replacing atleast one hydroxyl group by halogen, mostsuitably chlorine, and subjecting the resulting products to condensationor polymerization.

As initial materials for the preparation of the condensation products,monohydric or polyhydric alcohols of high molecular weight, as forexample stearyl alcohol, oleyl alcohol, cetyl alcohol, lauryl alcohol,myricyl alcohol, stearylene glycol or high molecular esters or ethersstill containing iree hydroxyl groups, such as ethyleneglycolmonostearyl ether, may be employed.

Prior to the condensation, the alcohols are treated with agents capableof exchanging hydroxyl groups in organic compounds by halogen, inparticular reactive chlorides, such as thionyl chloride, phosgene,sulphuryl chloride, phosphorus oxychloride, phosphorus trichloride orphosphorus pentachloride, or hydrochloric acid, if desired in thepresence of agents for removing water, such as zinc chloride andphosphorus pentoxide; the hydroxyl groups are thus replaced by 5halogen. The resulting halogenation products are then condensed in thepresence of condensing agents of the Friedel-Crafts type, as for examplealuminium chloride.

The condensation may be carried out in the presence of other organicsubstances, in particular hydrocarbon products, such as tars, mineraloils, their distillation, extraction and cracking products, orproductsfrom the destructive hydrogenation of carbonaceous'materials. Itis advantageous to condense the alcohols and thelike together withcyclic, preferably aromatic hydrocarbons. As the latter may be mentionedespecially naphthalene or mineral coal'tar fractions, such as crudebenzol, middle oil and anthracene oil as well as other products of an 5aromatic nature, as for example those obtained by destructivehydrogenation at elevated temperatures above 500 C. (so-called"aromatization) or dehydrogenation. Gaseous or vaporous olefines, suchas ethylene, propylene and butylene, 10

also in the form of cracking gases, and even liquid olefines obtainablefrom paraflinic hydrocarbons, as for example by cracking, may also bebrought into reaction during the condensation.

By adding the resulting condensation products 15 to lubricating oils andthe like, not only is the setting point of the oils, lubricating greasesor the like, lowered, but the temperature-viscosity curve is improved atthe same time. The amount of the products thus obtained to 20 be addedto the oils and the like to lower the setting point or improve thetemperature-viscosity curve may vary within wide limits, as for examplebetween 0.1 and 10 per cent or more. Even lubricating oils, gear oils orgear greases having very high setting points may be very considerablyimproved by the addition of the said condensation products.

The following example will further illustrate 30 the nature of thisinvention but the invention is not restricted to this example. The partsare by weight.

Example mt is freed from solid constituents of the reac- 5 tion mixtureby centrifuging, and refined with 2 'per cent of bleaching earth at from250 to 280 C., the light petroleum added as a diluent being thus partlydistilled over. After filtering oil the bleaching earth residue andsubjecting to steam"- 59 distillation in vacuo, about 50 parts'of lightlubrieating oil and about 40 parts of a cylinder oil having a viscosityof 10 Engler at. C. are obtained. If this be added in an amount of,about 1 per cent to a German machine oil hav 5 ing a setting point 01'zero C, the setting point of the oil is lowered to about 20 below zero0.

What we claim is:

1. The process of producing lubricants which comprises acting on analiphatic alcohol having at least 12 carbon atoms in the molecule with ahalogenating agent capable of exchanging a bydroxyl group by a halogenatom and acting on the resulting product with a condensing agent of theFriedel-Crafts type at a condensing temperature.

2. The process of producing lubricants which comprises acting on analiphatic alcohol having at least 12 carbon atoms in the molecule with ahalogenating agent capable of exchanging a hydroxyl group by a halogenatom and acting on the resulting product in the presence of an aromatichydrocarbon with a condensing agent of the Friedel-Crafts type at acondensing temperature.

3. The process of producing lubricants which comprises acting on analiphatic alcohol having at least 12 carbon atoms in the molecule with ahalogenating agent capable of exchanging a hydroxyl group by a halogenatom and acting on the resulting product in the presence of an aromatichydrocarbon with a condensing agent of the Friedel-Crafts type at acondensing temperature.

4. The process of producing lubricants which comprises acting on analiphatic alcohol having at least 12 carbon atoms in the molecule with ahalogenating agent capable of exchanging a hydroxyl group by a halogenatom and acting on the resulting product in the presence of an olefinewith a condensing agent of the Friedel-Crafts type at a condensingtemperature.

5. The process of producing lubricants which comprises acting on oleylalcohol with a halogenating agent capable of exchanging a hydroxyl groupby a halogen atom and acting on the resulting product with a condensingagent of the Friedel-Crafts type at a condensing temperature.

6. The process of producing lubricants which comprises acting on oleylalcohol with a halogenating agent capable of exchanging a hydroxyl groupby a halogen atom and acting on the resulting product with aluminiumchloride at a condensing temperature.

7. The process of producing lubricants which 10. An improved fluidlubricant consisting substantially of a major portion of viscous mineraloil containing waxy material in quantity suificient to affectsubstantially the pour point of the oil, and a minor portion of thecondensation product of naphthalene and oleyl alcohol, suflicient tolower substantially the pour point of the oil.

11. Process for producing a lubricant comprising treating an aliphaticalcohol containing a chain of at least 12 carbon atoms with ahalogenating reagent capable of substituting the halogen atom for thehydroxyl group of the said al- 001101, and treating the resultingcompound with a Friedel-Crafts condensing agent in the presence of anaromatic hydrocarbon whereby a condensation product of the aliphaticcompound and the compound containing the carbon ring is efiected.MATHIAS PIER.

FRIEDRICH CHRISTMANN.

